Triethylamine → (R)-N-Benzyl-2-chloro-N-(2-(6-(4-fluorophenyl)-4,5-dimethylpyridazin-3-ylamino)ethyl)propanamide

HRID 2093363노트

반응식

HRID 2093363 반응식
[CH2:1]([NH:8][CH2:9][CH2:10][NH:11][C:12]1[N:13]=[N:14][C:15]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[C:16]([CH3:19])[C:17]=1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:27][C@H:28]([CH3:32])[C:29](O)=[O:30].C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[CH2:1]([N:8]([CH2:9][CH2:10][NH:11][C:12]1[N:13]=[N:14][C:15]([C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)=[C:16]([CH3:19])[C:17]=1[CH3:18])[C:29](=[O:30])[C@H:28]([Cl:27])[CH3:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27245402-Chloropropionic acid, (+)-HCID 67320023N1-Benzyl-N2-(6-(4-fluorophenyl)-4,5-dimethylpyridazin-3-yl)ethane-1,2-diamine

생성물 1

HCID 58359251(R)-N-Benzyl-2-chloro-N-(2-(6-(4-fluorophenyl)-4,5-dimethylpyridazin-3-ylamino)ethyl)propanamide수율 74.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Sequentially treat a solution of N1-benzyl-N2-(6-(4-fluorophenyl)-4,5-dimethylpyridazin-3-yl)ethane-1,2-diamine (4.90 g, 13.98 mmol) in CH2Cl2 (70 mL) with (R)-(+)-2-chloropropionic acid (1.84 mL, 20.97 mmol), triethylamine (2.92 mL, 20.97 mmol), HOBT (3.21 g, 20.97 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.02 g, 20.97 mmol). Stir the resulting mixture at ambient temperature overnight. Wash the reaction mixture with saturated aqueous NaHCO3. Extract the aqueous layer with CH2Cl2. Combine the organic layers, dry over Na2SO4, filter, and concentrate under reduced pressure. Purify the residue by flash silica gel chromatography (20% EtOAc in hexanes) to afford the title compound as a yellow foam (4.59 g, 74%). ES/MS m/z 441.2 (M+1).

후처리

  1. washWash the reaction mixture with saturated aqueous NaHCO3
  2. extractionExtract the aqueous layer with CH2Cl2
  3. dry with materialdry over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. customPurify the residue by flash silica gel chromatography (20% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-7125993a82994698845e09efa4c8d118
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445493B2

반응 노트

불러오는 중…